Top 20 Pointed Toe Flats

Ballet Flats With a Point

I love shoes, but my feelings for pointy flats go well beyond love. I am obsessed with how they elongate the leg--let's face it, as fabulous as rounded ballet flats are, they can create stumpiness at times--and how they seem to hit a sweet spot where early sixties Aubry Hepburn intersects with John Hughes era Molly Ringwald. I love that spot!

Pointed toe flats can be surprisingly difficult to find, but judging from a recent browse through a fashion mag where I spotted three such shoes, there's hope on the horizon! Here, my current faves.

(photo: Do you like "toe cleavage," as offered by these red pointy flats from my collection? I kinda do, but not everyone feels that way. Luckily there are different styles that show varying degrees of toe...)

Rockport...

Kate Spade...

Always walking the line gracefully between retro cuteness and sleek modernity, Kate Spade offers at least a couple of gorgeous pointed toe flats every year.

There's a lovely shine to this first one, the "Gabe," in several perfect colors for the warmer months.

kate spade go

And how could I leave out this incredible tribute to NYC? Guaranteed to start conversations & draw compliments.

the bad news...

Pointy shoes are not the best for your feet. But we can take some comfort in the fact that pointy heels are worse than pointy flats! For best results, go barefoot at home to give your toes some breathing room.

How cool would this gently notched style look with pink, yellow or to break up an all-black look? It comes in all-black itself, too...

madden patent partial orsay

Black or nude patent and a partial Orsay look dresses this pair up for the office or a night out.

frye regina pointy flats

Frye...

I am a very lucky Frye boot owner but haven't tried their flats. If the boots are any indication, I'd expect quality & comfort from these shoes, which come in a whopping 19 colors, including this pretty "vintage turquoise."

Pointy flats from DV...

if you, like I, don't get around to pedicures very often, this shoe makes a very nice stand-in for a sandal. In black, nude, or several two-tone options -- my fave being this cute black-and-leopard number.

trump annulio

Ivanka Trump...

This shoe sits at the top of my wish list right now; the only problem is that I can't decide between the red patent & the pastel shades (this ubergirly pink and a mint tone) that are perfect for spring's pastel trend. At this big a discount, maybe both? ;)

Mia Pointed Toe Flats

For those of us who loved Mia's pointier "Hepburn" flat, which now seems to have been discontinued, the "Sweetness" is a nice consolation. And it's offered in 7 great colors like orange, plum &amp; cobalt, along with my favorite: this bright white that would totally pop with bright spring outfits.

Fine with a pointed style, but struggling with other comfort issues? Flats are known for poor arch support, so if you have a high-ish arch, that could be the problem. Try arch inserts, available at most drugstores. Flats with padded footbeds tend to be comfier, too.